Book Holiday Homes in Harpswell

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Featured Holiday Homes in Harpswell

Beautiful Oceanfront House- Stunning Water Views

Beautiful Oceanfront House- Stunning Water Views

Harpswell ME
Stay at this holiday home in Harpswell. Enjoy a fitness centre, a garden and laundry facilities. Popular attractions Thomas Point Beach and Brunswick Town Commons ...
Opens in a new windowBeautiful Oceanfront House- Stunning Water Views
Boothbay Harbor Woodland Retreat

Boothbay Harbor Woodland Retreat

Boothbay Harbor ME
Stay at this holiday home in Boothbay Harbor. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Carousel Music Theater and Boothbay ...
Opens in a new windowBoothbay Harbor Woodland Retreat
Centerview cottage

Centerview cottage

Harpswell ME
The price is NZ$816 per night from 18 May to 19 May
NZ$816
18 May - 19 May
includes taxes & fees
Stay at this holiday home in Harpswell. Enjoy free Wi-Fi, a garden and patios. Popular attractions Paddleworks and Mitchell Field are located nearby.
Opens in a new windowCenterview cottage
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Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE

East Boothbay ME
Stay at this holiday home in East Boothbay. Enjoy free Wi-Fi, a water park and a garden. Popular attractions Linekin Bay and Cabbage Island are located ...
Opens in a new windowSmuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE
5 Star Back Cove Apartment with water view!

5 Star Back Cove Apartment with water view!

Portland ME
Stay at this holiday home in Portland. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Thompson's Point and Maine Mall are located ...
Opens in a new window5 Star Back Cove Apartment with water view!
Downtown Waterfront Cottage with shoreline sitting room

Downtown Waterfront Cottage with shoreline sitting room

Boothbay Harbor ME
Stay at this holiday home in Boothbay Harbor. Enjoy a garden, cable/satellite TV service and an in-room coffee maker. Popular attractions Boothbay Harbor Memorial ...
Opens in a new windowDowntown Waterfront Cottage with shoreline sitting room
Rare West End Home • Walk to Old Port, Harbor View

Rare West End Home • Walk to Old Port, Harbor View

Portland ME
Stay at this holiday home in Portland. Enjoy a garden, in-room fireplaces and air conditioning. Popular attractions Thompson's Point and Maine Mall are located ...
Opens in a new windowRare West End Home • Walk to Old Port, Harbor View
Captain's Guest Room. Discover the authenticity & great value!

Captain's Guest Room. Discover the authenticity & great value!

Bath ME
The price is NZ$250 per night from 18 May to 19 May
NZ$250
18 May - 19 May
includes taxes & fees
Stay at this holiday home in Bath. Enjoy free Wi-Fi. Popular attractions Chocolate Church Arts Center and Bath Center for the Arts are located nearby.
Opens in a new windowCaptain's Guest Room. Discover the authenticity & great value!
Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Phippsburg ME
Stay at this holiday home in Phippsburg. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Sewell Pond Conservation Area and Georgetown ...
Opens in a new windowSummer 2026 ! Kayak on the Kennebec " EVERYTHING you need "
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Harpswell Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Harpswell vacation homes are the perfect way for you to wing it.

Holiday houses in Harpswell let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Harpswell in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Harpswell adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Harpswell with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Harpswell vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Harpswell Holiday Homes essential information

Accommodation
632 Holiday Homes
Lowest Price
NZ$250
Highest Price
NZ$816
Popular accommodation
Beautiful Oceanfront House- Stunning Water Views, Boothbay Harbor Woodland Retreat, Centerview cottage, Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE, 5 Star Back Cove Apartment with water view!, Downtown Waterfront Cottage with shoreline sitting room, Rare West End Home • Walk to Old Port, Harbor View, Captain's Guest Room. Discover the authenticity & great value!, Summer 2026 ! Kayak on the Kennebec " EVERYTHING you need "

Top trending hotels in Harpswell

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$417 per night from 25 May to 26 May
NZ$417
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, 3 coffee shops/cafes and breakfast (surcharge). Our guests praise the helpful staff and the ...
Opens in a new windowPortland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$304 per night from 26 May to 27 May
NZ$304
26 May - 27 May
includes taxes & fees
Stay at this spa hotel in Portland. Enjoy free Wi-Fi, a full-service spa and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowPortland Regency Hotel & Spa
Cambria Hotel Portland Downtown-Old Port

Cambria Hotel Portland Downtown-Old Port

3 out of 5
25 HANCOCK STREET Portland ME
Fully refundable
The price is NZ$335 per night from 25 May to 26 May
NZ$335
25 May - 26 May
includes taxes & fees
Stay at this business-friendly hotel in Portland. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the restaurant and ...
Opens in a new windowCambria Hotel Portland Downtown-Old Port
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HomeAwhile

HomeAwhile

2 out of 5
205 Southborough Drive Scarborough ME
Fully refundableReserve now, pay when you stay
The price is NZ$259 per night from 19 May to 20 May
NZ$259
19 May - 20 May
includes taxes & fees
Stay at this hotel in Scarborough. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Maine Mall and Thompson's Point are located ...
Opens in a new windowHomeAwhile
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.